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A0737

Sigma-Aldrich

N-acetylcysteine amide

≥98% (HPLC)

Synonym(s):

(R)- 2-(Acetylamino)-3-mercapto-Propanamide, AD4, N-Acetyl-L-cysteinamide, NACA, acetylcysteinamide

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About This Item

Empirical Formula (Hill Notation):
C5H10N2O2S
CAS Number:
38520-57-9
Molecular Weight:
162.21
MDL number:
MFCD01696115
UNSPSC Code:
12352209
PubChem Substance ID:
329770626
NACRES:
NA.25

Quality Level

100

assay

≥98% (HPLC)

form

lyophilized powder

storage condition

desiccated

color

white to off-white

solubility

H2O: ≥20 mg/mL
DMSO: >40 mg/mL

storage temp.

2-8°C

SMILES string

CC(=O)N[C@@H](CS)C(N)=O

InChI

1S/C5H10N2O2S/c1-3(8)7-4(2-10)5(6)9/h4,10H,2H2,1H3,(H2,6,9)(H,7,8)/t4-/m0/s1

InChI key

UJCHIZDEQZMODR-BYPYZUCNSA-N

Application

N-acetylcysteine amide has been used:
  • to protect retinal pigment epithelium (RPE) from oxidative stress
  • to show that increased expression of cell adhesion molecule 4 (CADM4) in oligodendrocytes inhibits myelination
  • to protect cells from apoptosis induced by shikonin plus erlotinib/gefitinib
  • as a component in various culture media

as an antioxidant to reduce oxidative stress in brains of homozygous Drosophila spermine synthase (dSms e/e) mutant flies and melanoma cells.

Biochem/physiol Actions

N-acetylcysteine amide is a membrane penetrating antioxidant with antiinflamatory activity through regulation of activation of NF-κB and HIF-1α as well as modulation of ROS. The compound readily crosses cell membranes, replenishes intracellular GSH, and defends the cell from oxidative stress. In contrast to DTT, AD4 is able to directly reduce intracellularl GSSG to GSH without the involvement of glutathione peroxidase. Such direct thiol exchange might have a protective effect. This compound has a potential in research and exploration for treatment of neurodegeneration, radiation exposure, and other oxidation-mediated disorders.

Other Notes

This product is hydroscopic and air sensitive.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Intracellular effects of atmospheric-pressure plasmas on melanoma cancer cells
Ishaq M, et al.
Physics of Plasmas, 22(12), 122003-122003 (2015)
Shikonin sensitizes wild-type EGFR NSCLC cells to erlotinib and gefitinib therapy
Li YL, et al.
Molecular Medicine Reports, 18(4), 3882-3890 (2018)
Oxidative stress-mediated NFkappaB phosphorylation upregulates p62/SQSTM1 and promotes retinal pigmented epithelial cell survival through increased autophagy
Song C, et al.
PLoS ONE, 12(2), e0171940-e0171940 (2017)
Spermine synthase deficiency causes lysosomal dysfunction and oxidative stress in models of Snyder-Robinson syndrome
Li C, et al.
Nature Communications, 8(1), 1257-1257 (2017)
Axoglial adhesion by cadm4 regulates CNS myelination
Elazar N, et al.
Neuron, 101(2), 224-231 (2019)
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